Gangster Sam
by applehead321
Summary: For Sam Winchester it was all gang fights, drugs, filthy hookers and street life, until his brother showed up…Then it all changed. Dean/OC Sam/OC
1. Chapter 1

Sam POV

I felt my face get crushed by my opponent's foot, and I fell to the ground whimpering. My opponent, Big Black Bill, had been fighting me for my hooker, Cinnamon Rose; she was new around here and not broken in, hell she was the only clean hooker around. I really wanted to be the first one to break her into the gang life, but now I'll probably never have a chance. Big Black Big spat on my bloody, broken face. I felt completely at loss and started to crawl away, crying. I heard jeering behind me as I attempted to leave.

"Hey you there, the one crying," I heard a deep voice behind me call.

 _Oh shit! I'm going to get shot!_

I started to crawl faster.

"No stop! I'm not going to hurt you!" The voice soothed. I stopped tired and ready to die. I turned around and what I saw brought all hope back into my street life.

"D-Dean?" I wheezed, "Is that really you? My big brother?"


	2. Chapter 2

Dean POV

I looked at my pathetic, drugged out, brother, and frowned.

"What the fuck happened to you?" I asked.

"Dean! Dean! Dean! Its really you… Man you have to get me out of here, I'm gonna die soon," He hacked, I noticed some of his teeth were missing. I shook my head and helped him up.

"Its alright little man, your coming with me," I helped him to the Impala, reluctant to let him into my beloved car.

"Hungry?" I asked.

"Yes! Can we go to Pizza Hut? Pizza! Pizza! Pizza!" He laughed joyfully. I was going to have trouble getting him off whatever he was on. I turned down a road and stopped at pizza hut.

"Buddy what're you on?" I asked after finding a table. He smiled squinting at me.

"I take crack mixed with anything I can find behind dumpsters," He stuck his tongue out at me. I sighed and turned to the road, driving quickly to the nearest Pizza Hut. Once there, I cut the engine and turned to my brother.

"Alright Sammy, we gotta set some ground rules if you're coming with. First off, no more drugs, hookers, gang fights, or anything like that," He frowned at me, his face falling. "And no more big black people," I shudder mentally at the horrific memory. I step out of my car and walk towards the double doors. Sam follows, slamming the door of my baby a little _too_ hard, and I turn to scowl at him. He looks down, his face greatly resembling that of a shamed child and I roll my eyes, turning back to the Pizza Hut. The sun beats down on us and I suddenly regret wearing the jacket, the leather bearing down on my shoulders. I tell Sam to go in and hand him a wad of cash, walking swiftly to the car to throw my jacket in. I suddenly hear a suspicious thumping from the trunk, and I stalk over to it, pulling a handgun from my waistband. Before I can reach it though, my trunk opens to reveal a large, dark brown, cleanly shaved head. My eyes widen as I realize what had happened.

"Big Black Bill?" The large head nods and a muscular chest appears from my trunk, supported by surprisingly thin legs.

"Hey," He waved meekly. "Ya know, whatcha did fer Sam back there was real nice. Y'all brothers?" I inconspicuously shoved the gun back into the waistband of my pants. This guy was tough, big, and had just beat the shit out of Sam, yet here he was, climbing out of my trunk, telling me I was nice.

"How did you get in there?" I questioned, my voice still hard. He shrugged.

"I live in Detroit, what didya expect?"

"And what the hell are you doing in my trunk?"

"Well, ya know, I thought maybe," he trailed off.

"Maybe what?" I urged him on.

"Well, maybe I could go with you guys to wherever you're going?"

My initial reaction was to say know, but then I thought about it. They yellow-eyed demon could have dad, and more muscle could always be helpful.

"Well, I guess we could see. You want some pizza?" His face lit up like a child on Christmas. I sighed, this wasn't my best idea. I crooked my finger in the universal "come with me" gesture and walked into the Pizza Hut. When Sam saw who I was with he immediately cowered back into the seat. Big Black Bill drew many strange looks, although he just brushed it off and waved to them.

"Dean? Is, is that,"

"Big Black Bill? Yes," I cut him off. He shoved himself as far into the booth as humanly possible. Big Black Bill just sat down at took Sam's trembling hand, shaking it enthusiastically.

"I'm Big Black Bill. Nice to meetya!"

 **Please review!**


	3. Chapter 3

Dean POV

Sam shivered looking at Big Black Bill, thankfully the shock of the big back man seemed to sober him up a bit.

"Sammy, what happened to you? You were going to Stanford! How did you end up here?" I asked wanting to get my facts straight.

"I don't know… I just got mixed up in everything and ended here… How did you find me? And why did you bother trying to find me?" Sam blurted.

"I just asked around, the reason I came was because dad is gone. I've been looking for him for six months. I figured you could help me, and Big Black Bill could help us out to," I explained. Sam nearly choked on his food.

"Big Black Bills coming!?" He yelped making everyone look at us. I smiled apologetically at them before turning back to Sam.

"Yes-"

"Wait, whao whoa whoa whoa. Whoa. Uh I neva said I'd help you find your dada," Big Black Bill chimed in. I shot him a killer glare, "Uh maybe I'll help you guys… If ya tell me what's goin on," He said nervously. I looked around to check if anyone was listening. My eyes rested on a suspicious looking man in the corner.

"Christo," I whispered. His eyes flicked black before returning to normal.

"I'll explain in the car," I said quickly before shoving my seat back and swiftly walking to my car.

"Do I havta sit in the back?" Big Black Bill whined, pizza sauce smeared all around his face. We did _not_ have time for this.

"Sammy get in the back," I ordered.

"But-"

"Get in the back!" I cut him off. He wordlessly obeyed and then we were out of there. I saw the demon following me from behind and knew I had to take it out.

"Alright Bill-"

"Call me Blackie," He smiled.

"Uh okay, Blackie, I'm going to stop the car and I need you to get that guy out of his car and hold him down for me okay?"

"Oh I don't know it sounds dangerous for Ol' Blackie," He whined.

"Just do it!" I barked slamming on the breaks sending Sam forward in his seat, awaking him. Without hesitation Big Black Bill leaped out of the car, ripped open the demons car door and held him down. I raced out after them and began chanting exorcism and pouring holy water on him.

"Who sent you?" I demanded to know.

"Your worst nightmare," He smiled.

"My worst nightmare is no pie and no girls, so I doubt they sent you," I growled pouring more holy water on him and chanting.

"Alright! The yellow-eyed demon did!" He squealed. I paused shocked he knew where I was, then snapped out of it, ending it for the demon. Black smoke exploded from the person's mouth and it was gone. I wiped my hands on my jeans and Big Black Bill-excuse me, Blackie- looked at me uncertainly.

"W-What was that?" he stuttered.

"A demon,"

 **Please give me reviews!**


	4. Chapter 4

Dean POV

"A what!?" Big Black Bill, ahem, Blackie muttered. I ran my hand through my dirty blond hair, groaning at the situation.

"A demon, I think our dad's tracking it," I replied.

"Wait, if there are demons then what else is out there?" he asked timidly.

"Mostly monsters, spirits, demigods, gods, demons, probably more," He looked at me cautiously. "If it helps at all, we haven't found any trace of Bigfoot or the Loc Ness Monster," I said sarcastically.

"And you guys hunt these things?" Well, at least he's a fast learner.

"Yeah," Sam piped in. "When I told my dad there was a monster in my closet he gave me a 44," I smirked a little at the memory.

"Well Sammy, what else could he have done?"

"Told me there wasn't?"

"Guys!" Blackie's voice brought us back to earth. We turned back to him, ignoring our little conflict for now. Well, at least Sam had sobered quite a bit.

"Yeah?" I questioned him.

"If you guys are good at hunting them, why do you need me?"

"We'll need all the help we can get," I replied grimly. My phone rang and I groped around in my pocket searching for it.

"Hello?"

"There's a werewolf down in Chicago,"

"Dad?!" I exclaimed, shock shooting through me.

"Yeah it's me, I need you to go down to Chicago and hunt that for me,"

"Where are you?" I asked. The line went dead and I slammed my phone shut. Two expectant faces met my gaze as I turned around.

"We're going to Chicago," I said adamantly.

Demon POV

"They're headed to Chicago," I spoke to the bowl of blood held between my palms. I rasp came back to me.

"Yes sir,"

 **Sorry it's pretty short, I'll post another one soon. Review!**


	5. Chapter 5

**So so so so so sooo sorry for the wait. I'll have to work on updating more often. Anyway, here is a new chapter. Special thanks to**  
 **yuzukikuran476 for reviewing. I'll try to get some other things updated within the week. Love you guys, :***

Dean POV

We crept silently into the dark building. I gestured for Sam and Blackie to follow me as I scanned the premises. A suspicious rustling noise behind me drew my attention. I held up my hand and stalked toward the noise.

"OW FUCK!" A loud scream came from around the corner. I slowly slunk over, peeking around the corner. A familiar girl lay in a pile of boxes, dressed in stockings, something that resembled a bikini and a pair of black stilettos. She huffed angrily to herself as she pulled off the heels and began walking towards me. She walked straight into my chest and screamed. She threw one of the stilettos at my head and proceeded to hit me repeatedly with the other.

"Hey, woah woah woah," I grabbed her arms to restrain her. "Calm down," She eventually relaxed. I head stifled laughter behind me.

"Don't laugh, she's vicious," I hissed at them.

"She's just a hooker Dean," Sam smirked.

"I'm. Not. A. Hooker." Her voice was soft but somehow caused my brother to cower in the corner.

"Yeah Sammy, just a hooker," I chuckled. She squirmed in my grip prompting me to release her. I let her go and stepped a few feet back cautiously.

"What's your name sweetheart?" I smirked suggestively, my eyes raking her body.

"Back off asshole," she shoved past me. "I have work to do,"

"You can call me whatever you like baby, but the name's Dean," She turned to say something, but she was interrupted by running into a wall.

"Oh god," She snarled.

"The name isn't god, but close enough," She rolled her eyes and jogged down the hallway,

"Whatever,"

"What's your name baby?" I tried one last time.

"Rose!" She yelled before disappearing down the hall. Blackie let out a low whistle, but I ignored him.

"Come on, there isn't a werewolf in here," they trailed after me. Our little trip was interrupted by a shrill screech.

"May the power of christ compel you!"

"Oh my god," I sighed, turning and running towards the feminine voice.


	6. Chapter 6

Dean POV

I charged around the corner, coming face to face with quite a peculiar sight. The hooker named Rose was backed against a wall, hitting a snarling werewolf with a shoe, and yelling obscene things at him.

"Back away you heathen!" she screamed, batting at it with the heel of her shoe. I yanked the gun out of my waistband and popped three silver bullets into the ugly thing's head. She turned around, her stiletto still raised. I gave her a skeptical look.

"You're a hunter, yet you dress like a hooker and use shoes against werewolves?" She managed to look sheepish and detached herself from the wall.

"I'm not a hooker," she folded her arms in front of her.

"Then why dress like one?" I felt my eyebrow quirk in disbelief.

"A certain lead told me that the werewolf may have been connected to some of the gangs. And from what I remember, those gangs are quite fond of hookers," Well to give her some credit she had a point about gangs and hookers.

"Well, take some advice sweetheart. Next time you hunt a werewolf, use silver bullets. Not shoes," I signaled to Blackie and Sam and began walking towards the door.

"Wait!" I turned to look at her. She shifted uncomfortably, looking to the ground. "Can I uh, get a ride?"

"Don't you have a car or something?" I asked.

"Well not exactly…" I groaned. My poor Baby shouldn't have to carry hookers. On the other hand I wasn't about to not give a ride to the skimpily dressed wannabe hunter.

"Fine, let's go,"

The motel room had two beds, but there were now 4 people in our little rag tag band. Against my will, we had adopted a hooker. Sam and Blackie sat on a bed, playing a game of Nigger Cars, whatever that was. Rose was in the bathroom taking a shower. And I was trying to ignore the obnoxiously high Metallica lyrics blaring from the bathroom and the shouts of victory from the bed next to mine. My thoughts were interrupted by a soft voice. I realized the water had shut off and the singing had stopped.

"Dean!" she hissed again. I sighed, sliding off my bed and walking to the door.

"What?" I groaned.

"I don't have any clothes,"

"Just wear the hooker outfit," I heard her grumble something under her breath.

"As much as I love dressing like a prostitute, the damn thing is torn beyond belief,"

Sarcasm tinged her voice. I could always force her to come out naked, or dressed in a torn bikini, but there was some little voice in my head nagging me to be nice for once.

"Ok, fine, hold on," I sifted through my duffel, grabbing a hoodie and a pair of sweatpants.

"Here," the door opened a crack and she grabbed them quickly.

"Thanks Dean," I nodded, even though I knew she couldn't see me. A slight creak

alerted me to the bathroom door opening. She slunk out, the hoodie drooping from her shoulders down to her knees. The sweatpants were probably tightened to extreme measures, which by the way she stopped every few feet to pull them up probably wasn't enough. She walked carefully over to where she laid her duffle, laying on the floor with it under her head. Sam and Blackie were already asleep, both sprawled over the tiny bed. I laid back, trying to ignore the girl lying on the dirty floor. When I couldn't sleep, I rolled over to see if she was. Her rowan hair was sprawled over her duffle and her slate gray eyes seemed to be mapping the ceiling. I leant down and nudged her arm. Her gaze shifted over to me. I slid my body across the bed and patted the side closest to her. She gave me a questioning look.

"Just stay on your side," she flopped down, bouncing the bed.

"Thanks," she muttered softly, hugging a pillow to her chest. Soon after I fell asleep. In a crappy hotel room. Next to a hooker.


	7. Chapter 7

Dean POV

"Let's get one thing straight, aiight? I ain't some washed up hooker," Rose began for the tenth time, "I'm a _hunter_. Just like you, Winchester," I scoffed as the fiery red-head pulled up the waistband of my sweatpants up her narrow hips.

"Right. How'd you get in the business anyway?" I asked with sincere curiosity. She scowled at me under her feathered bangs.

"None of ya business," I threw my hands up.

"Just trying to get to know you," She remained silent and glanced away. I saw this conversation was going nowhere and sat up to wake up Sam and Blackie. Her head jerked upward when she saw me leaving and cleared her throat. I stopped and met her eye. It was still unreadable, though she seemed to have softened.

"Listen, if you tell _anyone_ you're dead. _Dead._ And you can't go crazy or-"

"I got it!"

"Right. Okay, so my dad was a deadbeat and mom was a druggie. Great origin story right? Real original. I was eleven when my little sister, Roxie, was born. I had to take care of her and my mom until I was sixteen and ma OD'd on **meth**. It wasn't so bad growing up around here. I worked at a diner for a while but when that ended I had to working at a gas station. It was rough, not much money. By the time Sul came around Lily and I were sleeping in the allies. He said he could help us. He said… he said Roxie was special. That she was young and would be able to carry something called Lilith. I told him to eat shit. The crazy old fuck said that we could control the world with the powers he could give Roxie. At that point I didn't know what to say, ya know? Before I knew it black smoke was pouring out of his mouth and into Roxie's. Sul was dead and Roxie… Roxie wasn't Roxie anymore. We went to dozens of people and eventually I got the full scoop on the demons and supernatural shit. She's been fighting against this _thing_ inside her for over year before she couldn't fight anymore. The thing, Lilith took over one night and nearly killed me. I came to the next day and she was gone," Oh wow okay. I was expecting a werewolf to mug her, or maybe a vampire boyfriend. She cocked her head at me,

"What about you?" she asked.

"Mom was killed by a demon and now my dad's chasing around this demon trying to kill it ever since I was 4," I ran a hand over face. "We gotta find him, he's been gone for six months,"

"Rough," she offered a sympathetic smile. "Sorry 'bout your mom and all that,"

"Yeah. Sorry about your sister," I returned the gesture.

"Ah no worries, I gotta plan to get her back," she grinned. I was going to ask her about this 'plan' when Sam came walking in. Rose retreated to the bathroom.

"So...You really came back for me huh?" Sam asked. "Not just some weird crack dream? I could've used your help eight missing teeth ago," Blackie sprinted into the room and chucked a vase at Sam's face,

"Make that nine missing teeth," He laughed gleefully. Sam snarled and threw a shard at Blackie.

"Guys," I warned, "Knock it off. We have long day ahead of us, we need to conserve our strength," Rose poked her head out of the door.

"We do? What's the plan, boss-man?" She kicked away shards of glass in her path.

"Getting out of here," I said slowly. Though I wasn't sure what the plan was. She shrugged a bit then sauntered over to me.

"I have a lead, possibly. Why don't you let me take the reins for a bit," She grinned. I was about to say the hell with that, I barely know you but looking at her face I knew she could be trusted.

"Alright Cinnamon, lead the way,"


	8. Chapter 8

Sam POV

I writhed on the cold seat of the Impala. Fuck, this was bad. I guess all those drugs are really kicking me in the ass. At first I felt better, maybe because my brother was here, maybe because we were going to find Dad, but mostly because I had finally kicked the drugs. Then this happened. Sweat poured out of me, coating the leather. I felt like my head was going to explode. Rose were happily cuddled up in the seat next to me, and Blackie was chatting animatedly with Dean. I groaned in aggravation and threw a heavy arm over my eyes. Maybe if I could get just a little bit of coke, just a little, that way I wouldn't be going totally cold turkey. No! What was I thinking? My eyes flicked up to Dean. I can't go back to that, it would tear him apart. Not to mention then the withdrawals would be worse. No, I won't do any more drugs. I can tough it out. I'm a Winchester.

Rose POV

Dean hummed along to some rock song I didn't recognize, Blackie had fallen asleep, and Sam was sitting next to me silently. He really didn't look so good. I felt a twinge of guilt. I shouldn't do this, these people are so kind. Dean turned to me,

"You doin okay? You don't look so chipper," I forced a smile.

"I'm good," He nodded and turned back to face the road. "Dean?" I asked.

"Yeah?"

"You would do anything for your brother right? Like anything?" I made eye contact with him in the mirror.

"Well," he seemed to pause and think. "Of course I would do anything in my power to protect Sam...but there are limits. I mean, I don't think I could put anyone else I cared for in danger," I nodded. That made sense.

"Dean?" He looked back again.

"What now?"

"I don't think this is a good idea," I mumbled.

"Not the best time for second thoughts sweetheart. We're here," He grinned, moving to open the door.

"NO!" I yelled. He looked taken aback. "Dean. Do not get out of this car!" My voice held desperation. He gave me a confused glance.

"Rose, I thought you said this was a lead. For yellow eyes. I need to find my dad," Sam and Blackie stepped out of the car beside him. Shit, this is not good.

"UNLEASH THE HOUNDS!" A deep voice bellowed.

"DEAN! GET IN THE CAR!" I screamed. It all happened so fast. A pack of massive wolves sprinted from the old warehouse. I was frozen to my seat. I could only watch as Sam, Dean, and Blackie turned to run for the car. A wolf lunged for Blackie, clamping its jaws around his unstable legs and throwing him to the ground. A cry of pain split through the air. Dean roared as he grappled with a wolf that clawed at his vulnerable neck. Sam ripped the door of the car open, and I reached for his hand to pull him in when another wolf leapt onto his back and dragged him away. I could see blood trickling from him as the wolf dug its claws into his back. Blackie screamed in pain, but he managed to cross his legs around the wolf's neck and snap it in one swift motion. He threw himself into the door that Sam had left open and slammed it shut. Sam and Dean had no such luck. I watched Yellow Eyes stroll out from the darkness, his small army of demons following. They called off the wolves, forcing Sam and Dean to their knees. When Yellow Eyes grinned at me, I realized that he had never intended to help my sister. But that wasn't the worst part. The worst part was the look of searing betrayal in Dean's eyes. I swallowed the lump in my throat and spun the car around, driving out of danger.


	9. Author's Note

Hey! So sorry we've been inactive again! Family trouble :( Well what do you guys think? My friend has totally covered this one in lemons...yet... Please review, let us know what's good and what we can fix!


	10. wolfafter math

Note-I'm sorry to change this up, but hey, this is called Fanfiction for a reason! So, in our little AU, demons can be killed with guns, knives, etc. It's just a lot harder to kill them than it would be to kill a human. Capeshe?

Rose POV

"What the fuck were you fucking thinking?!" Blackie bellowed. "Do you realize what you just did?!" I hung my head in shame.

"Yeah, that's fuckin right! Only thinking about yourself huh? Fucking bitch!" he yelled.

"Blackie!" I interrupted.

"What now? You gonna throw me outta dis car?" he snarled.

"Ugh no!" I groaned. "I have a plan," He rolled his eyes.

"Oh yeah, because your first plan worked out _sooo_ well,"

"Please just let me do this," I pleaded. "I mean, I can't screw things up much more, can I?" His eyes softened.

"All right, what're we gonna do now?"

The Impala rolled up in front of the warehouse.

"Ok, here," I held a pair of handcuffs out to Blackie. "Put these on," He held out his hands and I cuffed him.

"Ready?" he asked me.

"Yeah," I nodded. "Ready," I drug him struggling out of the car and into the dark warehouse.

"Azazel!" I yelled. "I got a little somethin for ya!" He materialized from the darkness.

"Oh hello again my pretty rose," his cold hand slid down my cheek. "And why would I want this?" he gestured towards Blackie.

"He's valuable to the Winchesters," I tilted my head towards the brothers chained to the wall. "Hurt him, and it will hurt them more,"

"Let him go, you evil bitch!" Dean roared, thrashing in his chains. Azazel's face twisted into a grimace that resembled a smile and took the cuffed man from me. As soon as Blackie left my hands, he ripped the cuffs open, slid two knives into his hands, and swung them up to decapitate the yellow eyed demon. I pulled my favorite machete from my waistband and stabbed a henchmen a few times in the chest. Adrenaline rushed through my veins as I bobbed and twisted, killing demons as I went. There were a few left, but Blackie could handle them, so I rushed over to the restrained Winchesters. After helping them out of their bonds, I started to drag them towards the door.

"Guys, we need to go! There'll be more any second!" Dean ripped his hand from mine.

"And why would we trust you, you got us into this whole mess!" His words were so full of venom I could almost feel the sting.

"Fine, then just go," I pointed outside. "Your car's out there," He nodded and turned to walk away when another voice spoke.

"What a pleasant surprise," The silky tone drove shivers up my spine. "Nice to see you again, _sister_ ," I turned around slowly. The Winchesters had halted, perhaps sensing the danger.

"Roxie please," I pleaded. "Fight it, I know you can," She smirked at me.

"Oh Rosy, Rosy, Rosy," She traced a finger down my arm. "I'm not even Roxie anymore, she's dead. It's Lilith now," She eyes raked over Blackie, who was approaching slowly. The shell of Roxie nodded towards him. Two ragged demons grabbed him and yanked my backwards.

"Kill him," Roxie snarled. Rose recoiled.

"No- no Roxie, please- please you don't have to do this," The ball in my throat caught my words and distorted them.

"Do it, or you 'whittle sister will-" The image of my little sister slitting her chest open burned my eyes, "Die. And I'll have to take over someone else's body. It's a lot of trouble you know," I glance at Blackie. He couldn't fight anymore. It was run ragged, it would be easy. Rose pulled herself and glanced and Dean and Sam. Dean's hand was on his gun, ready to pull it out but Rose knew what she had to do. She looked at the bloody machete in her hand and in a swift motion run it through Roxie's heart. The demon's eyes flashed with rage and shock. There was a whiff of black smoke and it spun into the air and flew into on of the dead body on the floor. I watched in horror as Roxie looked up at her with big blue pools of purity.

"Rose?" She wheezed. Her eyes rolled down to the machete in her chest, "Thank you- it's gone," Roxie fell backward into a puddle of her own blood. I flung myself over her body.

" _No,"_ a sob ripped through me, " _NO!"_ She was still in there. I just killed my own sister.

Hands pried me away from Roxie's limp body. I twisted, claws, bite, did whatever I could do to get away. A sick crunch filled my ears as one of them punched my jaw and the blackness took over.


End file.
